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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 123 Vacation Homes in Sudlersville with updated reviews, rates, and availability.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Miscellaneous

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Miscellaneous

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.8 out of 10, Exceptional, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is SAR 2,115
SAR 4,151 total
includes taxes & fees
28 Mar - 29 Mar
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront family resort Lodge with private pier, game room and bar
Game room

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (25)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar
Gorgeous Creek Side Ranch-Style Estate With Dock
Fridge, microwave, oven, stovetop

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Terrace/patio

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (75)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
Fridge, microwave, oven, stovetop

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun loungers, beach towels

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
A heated pool

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (33)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (2)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is SAR 657
SAR 1,018 total
includes taxes & fees
28 Mar - 29 Mar
BAYSIDE BUNGALOW
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (10)
"Beautiful and it was located close to my daughter and her family. It is close to shopping both food and outlets. The morning view of the water was so relaxing and beautiful while having a cup of coffee. There was plenty of room for 4 adults and two kids. I will definitely stay here again. "
River Front, Private Single Family Home
Stay in the landmark Lighthouse!
Beach

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (96)
"Great views, unique living space and all the amenities. Really enjoyed our stay!"
Stay in the landmark Lighthouse!
Entire Townhouse in Rock Hall
Fridge, microwave, oven, stovetop

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (27)
"Property was located about 500ft from my sister and brother in laws house...sister is going through home hospice..so it was really convenient "
Entire Townhouse in Rock Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Sudlersville

Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is SAR 368
SAR 592 total
includes taxes & fees
28 Mar - 29 Mar
First Floor Studio Apartment in Historic Chestertown
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (33)
"The property is just stunning. We went in February, and i can only imagine how beautiful it is in the summer. The host had great communication. My family of 20 takes a trip every year. This is the best stocked house we have ever been to. The 3 kitchen spaces with a huge selection of pots and pans made meal prep a dream. The coffe station with sugar and creamers and Keurig pods was awesome. I cant say enough about this place. The layout is a little weird, one of the bedrooms is only accessable...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.